@nottelling, we are looking at moving for the winter to a warm place (for me) but not too warm (for my Canadian wife) to balance out our East Coast home. We spent a fabulous time last winter living on a houseboat in Sausalito and will do so again, perhaps a bit longer, this winter.
We’re going to try to pass on our house in the Boston area to another deserving family and replace it with a house designed for the next twenty years. We have a reasonably nice but not super-fancy 5 BR home in walking distance of an school in an affluent town with a good school system (the NY Times graphic article on education said that our school’s students were 3.2 years ahead of the national average at whatever age they measured). Lots of stairs (not great for aging), big yard, walking distance to nice town center, train to city, etc. I feel like we are stewards of this house for the next family with a few kids just about to enter elementary school. We’re going to try to find/build a smaller house on water (my wife is a painter who excels at painting water). It needs to be green or at least low allergy/mold as she seems to have been having a strong reaction to mold/allergens in our house/area since Hurricane Sandy if not before. Looking for one-level living for us plus perhaps a second floor when folks visit.
Neither ShawWife nor I intend to retire. We both love what we do. I can do it from most places that are near a major airport. I will probably want to travel less than I do now when I am in my 70s or late 70s assuming my health stays good until then. I will probably try to shift my mix of work to include more pro bono projects. I was a professor early in my career at a first-tier university and am reasonably well-known and could probably teach at a second-tier one now if I wanted, but not sure I do (I teach one week a year at my old university and am now starting something similar at Oxford). For both of us, we’ll keep doing what we love doing until we are forced by health issues to stop. So, a big preoccupation for us is/should be maintaining health.
ShawSon is in grad school in the Bay Area and probably will stay there as he is interested in tech startups. ShawD is going to look for a job as a nurse practitioner when she returns from a 3 month trip to SE Asia after an intense 5 years of BSN/MSN/jobs. Portland OR, Portsmouth NH and Northampton MA are in consideration, but who knows. She approached me last year and said (at age 22), “Dad, I have a, deal for you. When I figure out where I am going to live for the longer-term, you help me buy a two-family house. I will live upstairs and you can live downstairs. When I have kids, you and Mom can help with the kids and when you get old, I will take care of you.” I said “Sweetheart, you have a deal.”
Given all of that, we will have a retirement-friendly house in the Northeast because a) my wife is very tied to her community here (but is a social dynamo and can build friendships anywhere); and b) I retain a connection with the university I used to teach at many years ago that remains stimulating intellectually and helpful to my business. We will rent or buy a place in Northern California. We will help our D with the 2 family house idea if it comes to fruition. And, we own half of a Canadian house – and if Trump wins, ShawWife says we are moving to Canada (not a bad thing from a health care standpoint as we age anyway). So, we’re either going to have to hire a property manager and do AirBnB or start to shed houses at some point. If both kids end up West Coast, who knows, we may well move there for a greater part of the year.
Our plan covers the go-go and slow-go years but not the no-go years. I haven’t thought about that yet. We are remarkably active (I make one to two European trips a month plus fly to other places as well). We have a very active social life (ShawWife’s doing and cooking both very important there). We travel for vacations (last month we were in London/Berlin/Leipzig/Paris on one trip and Calgary/Canadian Rockies on another). I am trying to write one book and have another project to put out a 10th anniversary edition of another that the publisher wants to relaunch as it has done pretty well. I have built the slow-go years into my plans, (the one-level house, the reduction in travel) but I can’t really imagine the no-go years (and in fact they frighten both me and my wife).
So, our criteria:
Sort of warm in winter, beautiful in summer/spring/fall
Near good airport
Place where people are intellectually alive (this is important for both of us)
Might imply near a university but not necessary as I enjoy the buzz of the Bay Area VCs
Decent community of working artists
Place where we have or can build a community of interesting and nice people
Walking distance to town center
Easy access to outdoor recreation (cycling, kayaking, hiking, etc.) – ShawWife would love swimming too
I should worry about taxes but probably won’t
Access to good medical care
Near the kiddos
One of our places should be a place the kids would want to bring the grandchildren for extended trips
Note: grandchildren don’t yet exist and don’t appear to be close as neither kid is at that stage